Methods for production of terephthalic acid from ethylene oxide

• US 9,719,037 B2
• Filed: 06/30/2016
• Issued: 08/01/2017
• Est. Priority Date: 07/01/2015
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Sookraj, Sadesh H.
• Primary Examiner(s): Katakam, Sudhakar
• Assistant Examiner(s): Sawyer, Jennifer C
• Application Number:
  US15/197,838
• Publication Number:
  US 20170001940A1
• Time in Patent Office: 397 Days
• Field of Search: None
• CPC Class Codes: C07C 1/24 by elimination of water
• CPC Class Codes: C07C 11/04 Ethylene
• CPC Class Codes: C07C 51/416 Henkel reaction and related reactions, i.e. rearrangement of carboxylate salt groups linked to six-membered aromatic rings, in the absence or in the presence of CO or CO2, (e.g. preparation of terepholates from benzoates); no additional classification for the subsequent hydrolysis of the salt groups has to be given
• CPC Class Codes: C07C 63/26 1,4 - Benzenedicarboxylic acid
• CPC Class Codes: C07D 301/03 by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
• CPC Class Codes: C07D 307/60 Two oxygen atoms, e.g. succinic anhydride
• CPC Class Codes: C07D 307/89 with two oxygen atoms directly attached in positions 1 and 3
• CPC Class Codes: C07D 493/18 Bridged systems
• CPC Class Codes: C10J 2300/0916 Biomass
• CPC Class Codes: C10J 2300/1656 Conversion of synthesis gas to chemicals
• CPC Class Codes: C10J 3/00 Production of combustible gases containing carbon monoxide from solid carbonaceous fuels destructive distillation processes C10B
• CPC Class Codes: C10J 3/72 Other features
• CPC Class Codes: Y02E 50/30 Fuel from waste, e.g. synthetic alcohol or diesel
• CPC Class Codes: Y02P 20/52 using catalysts, e.g. selective catalysts

Abstract

The present invention provides methods for the production of terephthalic acid and derivatives thereof using ethylene oxide, carbon monoxide and furan as feedstocks. The process is characterized by high yields and high carbon efficiency. The process can utilize 100% biobased feedstocks (EO via ethanol, CO via biomass gasification, and furan via known processes from cellulosic feedstocks).

Claims

1. A process for making a chemical product comprising an aromatic diacid or derivative thereof comprising the steps of:

a) treating biomass to produce ethanol;

b) treating biomass to produce carbon monoxide;

c) converting the ethanol to ethylene oxide;

d) contacting ethylene oxide with the carbon monoxide in the presence of a catalyst to form succinic anhydride;

e) oxidizing the succinic anhydride to provide a compound selected from the group consisting of;

maleic anhydride, maleic acid, fumaric acid, a mono- or di-ester of fumaric acid, a mono- or di-ester of maleic acid, a mono- or bis-salt of fumaric acid, a mono- or bis-salt of maleic acid, and a mixture of any two or more of these;

f) contacting the compound of step (e) with furan to provide a compound containing a cyclohexene ring;

g) dehydrating the compound containing the cyclohexene ring to provide at least one of an aromatic acid anhydride, an aromatic diacid, a mono- or bis-salt of an aromatic diacid; and

a mono- or bis-ester of an aromatic diacid as the chemical product.

2. The process of claim 1, wherein at least one compound provided by oxidizing the succinic anhydride is maleic anhydride.

3. The process of claim 1, wherein at least one compound provided by dehydrating the cylcohexene ring is phthalic anhydride.

4. The process of claim 1, further comprising the step of converting the chemical product of step (g) to at least one of terephthalic acid, a mono- or di-ester of terephthalic aid, a mono- or bis-metal salt of terephthalic acid.

5. The process of claim 1, wherein the step of oxidizing the succinic anhydride is performed in a continuous flow reactor.

6. The process of claim 5, wherein the step of oxidizing the succinic anhydride is performed over a solid catalyst.

7. The process of claim 1, wherein the step of contacting the compound of step (e) with furan is performed in a continuous flow reactor.

8. The process of claim 7, wherein the step of contacting the compound of step (e) with furan is performed over a solid catalyst.

9. The process of claim 1, wherein the carbon monoxide is derived from biomass gasification.

10. The process of claim 1, wherein the furan is derived from a biobased feedstock.

11. The process of claim 1, characterized in that a carbon efficiency of the process is greater than 80% where carbon efficiency is calculated by:

determining the number of carbon atoms contained in a mass of aromatic diacid produced by the process, dividing that number of carbon atoms by the total number of carbon atoms fed to the process in the form of ethanol, carbon monoxide and furan to produce that mass of aromatic diacid.